Building Wealthfront and Benchmark Capital - Andy Rachleff

My great passion is product-market fit ... It's something that I find is the absolute key to success of a business, and I constantly try to figure out how to do a better job of finding it. And one of the things that's really clear to me is that if you don't find product-market fit immediately, you don't change the product; you change the market. You iterate on the market; you don't iterate on the product.

Something like less than 10% of professional investors outperform the market over five years—and those are people who are doing it for a living every single day, so what makes an individual investor who's doing it with their spare time think they can outperform the market.

I don't think that you should improve your weaknesses. I think you hire to your weaknesses. I think you should double down on your strengths.

Nothing about good investment feels right ... It does not feel right to invest when the market goes down and to sell when the market goes up, but that's how you make money. Literally, nothing about good investing practices feels right, and that's why almost everyone is terrible at it.

I've been teaching technology entrepreneurship courses at Stanford Graduate School of Business, and literally, my parting advice to my students in every class is 'If there's one thing that you can do, it's keep on learning.'

If you look at really successful people, they didn't become successful by being good at everything; they became successful because they were superb at something.

Product-market fit is just a fancy way of saying you've proven your value proposition. And how do you know you've proven it? Well, in a consumer company, its exponential organic growth. So, if we don't achieve exponential organic growth right away, we iterate on the market. Building more features doesn't ever get you fit. That's the mistake that entrepreneurs continuously make.

The CEO is seldom... the smartest person in the room, but they're usually the one with the best judgment. What's judgment? It's decision-making under uncertainty. Anyone can make decisions if they have all the data. The most impactful decisions in a business are usually the ones that are made under uncertainty.

Venture capitalists are not visionaries. Quite the opposite—they're opportunists. We don't try to predict what's going to happen; our job is to recognize a great vision when we see it. It's the entrepreneurs who are the visionaries.

One of my concerns with young CEOs today is they want to focus on product, but they don't actually want to lead people ... You can't be a CEO unless you want to lead.

Successful individuals, I find, are incredibly intellectually curious and built to learn.

I am very much anti-blog because people tend to revise history and write blog posts that make themselves look good, or they have never had any success in their life, but they're really good writers, and people mistake that for knowing what they're talking about.

I prioritize passion over talent if they have enough talent. The person who is passionate about the opportunity is likely to invest more time learning.

What I find is that people who work for a very successful company come to understand [what the keys to success are], and they look for that in their next employer. Someone who's worked for two unsuccessful companies has no idea what to look for, and they generally, as a result make a decision based on compensation, which only dooms them to fail again.

Burt Malkiel likes to say 'You cannot time the market, so don't even try. Just focus on the three things over which you do have control, which are diversification, minimizing fees, and minimizing taxes.'

Every industry, when it gets started, has very modest capital requirements. You used to be able to start a computer company for $1 million. You can start a disk drive company for less than $1 million. It's as the industry or market matures that you need more and more capital to gain an advantage.